The 15 Song Album collection:

[DaveCan]

I like it Dave, ok Titles or Songs with blah blah blah

Seemed to fit all the criteria you listed: "Titles with ambiguous/unconventional/challenging meaning/interpretation", via the title but it's also in the lyrics of that song.. In my understanding of ambiguous and a challenging meaning, interpretation etc, I figured a "hotel California" could fit the bill.. You can nix it if you'd like, your thread.

 

[HollowState]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto

 

[Cal Weldon]

Perfect: I think this Jimmy entry is as good if not better than any other so far.

01 - The Man Who Sailed Around His Soul - XTC https://youtu.be/e2EshWuC6lw
02 - Soul Bossa Nova - Quincy Jones - https://www.youtube.com/watch?v=T5ALPzS0QfQ
03 - Reaching For The Best - The Exciters https://www.youtube.com/watch?v=NUdNzP9PgqE
04 - Landing In London - 3 Doors Down https://www.youtube.com/watch?v=rguhxKEBlr4
05 - Back in 74 - Goblin Rebirth (https://www.youtube.com/watch?v=vdnzObrZPsU)
06 - In The Navy - Village People
07 - I Can't Tell You Why - The Eagles
08 - Anywhere Out Of The World - Dead Can Dance - The Missing 007 Theme
09 - Doo-Bop - Miles Davis https://www.youtube.com/watch?v=DZ1k_BrA8CI
10 - Trans-Europe Express - Kraftwerk https://m.youtube.com/watch?v=XMVokT5e0zs
11 - Surfing in a Hurricane - Jimmy Buffett - https://www.youtube.com/watch?v=xIGp6N19Vrw

 

[wintermute]

Ummm I think you just went through a time warp Cal

Tony.

 

[Flied Egg]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles

 

[gasboss775]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd

 

[Konzentr8]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline

 

[soundbrigade]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters

 

[wintermute]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News

 

[bendyha]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News
11 - 81 Poop Hatch - Captain Beefheart

 

[Sorento]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News
11 - 81 Poop Hatch - Captain Beefheart
12 - Desolation Row - Bob Dylan

 

[Cal Weldon]

Ummm I think you just went through a time warp Cal

Ya, what happened there, was I drinking or something?

 

[Konzentr8]

Glitch in the Matrix Cal

 

[MartyMG]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News
11 - 81 Poop Hatch - Captain Beefheart
12 - Desolation Row - Bob Dylan
13 - Windowlicker - Aphex Twin
Turns the rap video genre inside out & upside down. Hilarious and disturbing.
https://youtu.be/UBS4Gi1y_nc

 

[scottjoplin]

whoa challenging ha ha

 

[AstroZon]

Ya, what happened there, was I drinking or something?

Hopefully

 

[soundchaser]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News
11 - 81 Poop Hatch - Captain Beefheart
12 - Desolation Row - Bob Dylan
13 - Windowlicker - Aphex Twin
Turns the rap video genre inside out & upside down. Hilarious and disturbing.
https://youtu.be/UBS4Gi1y_nc
14 - She Talks to Angels - The Black Crows

 

[Cal Weldon]

01 - Glad To Be Unhappy - Eric Dolphy
02 - Hotel California - The Eagles
03 - Surfing on a Rocket - Air
04 - Cruel to be Kind - Nick Lowe
05 - Sci-Fi Wasabi - Cibo Matto
06 - I Am The Walrus - The Beatles
07 - Several Species of Small Furry Animals Gathered Together in a Cave and Grooving with a Pict - Pink Floyd
08 - Three Cigarettes In An Ashtray - Patsy Cline
09 - The Bravery of being out of Range - Roger Waters
10 - Hip To Be Square - Huey Lewis And The News
11 - 81 Poop Hatch - Captain Beefheart
12 - Desolation Row - Bob Dylan
13 - Windowlicker - Aphex Twin
Turns the rap video genre inside out & upside down. Hilarious and disturbing.
https://youtu.be/UBS4Gi1y_nc
14 - She Talks to Angels - The Black Crows
15 - If The Phone Doesn't Ring It's Me - Jimmy Buffett

 

[Cal Weldon]

Songs with a reptile in the title.

Crocodile - Jimmy Buffett

 

[AstroZon]

01 - Crocodile - Jimmy Buffett
02 - Chameleon - Herbie Hancock